Earlier in my career, I spent a lot of time trying to find the right answers. Looking back, I think I would have benefited from spending more time figuring out which questions were worth asking in the first place.
I do not say that because I regret the path I took. My career has moved through several different stages, including financial markets, entrepreneurship, real estate, and mentoring small business owners. Each experience taught me something that I probably could not have learned any other way. What has changed over the years is what I pay attention to and what I consider important before making a decision.
When I was younger, I tended to believe that a good opportunity deserved my attention simply because it was a good opportunity. I thought moving quickly showed confidence, and I often assumed that a busy schedule meant I was making progress. Some of those instincts helped me, but experience eventually showed me that there were other questions I should have been asking.
Today, I spend much more time thinking about people, priorities, patience, and whether something genuinely deserves my attention.
Who Am I Actually Working With?
Earlier in my career, I probably paid more attention to the opportunity than to the people involved. If the business case made sense, I assumed we could figure out everything else along the way.
I see that very differently now. The people involved in a project can completely change the experience of working on it. A relatively ordinary project with thoughtful and dependable people can be incredibly rewarding. An exciting project can become unnecessarily difficult when the people involved have different expectations about communication, responsibilities, or how decisions should be made.
I have also learned that you discover much more about people when something goes wrong. Almost everyone is easy to work with when the project is moving smoothly. The useful information comes when there is an unexpected delay, a disagreement, or a problem nobody anticipated. I pay attention to whether people communicate openly during those moments and whether everyone immediately starts assigning blame or begins looking for a solution.
I wish I had understood earlier that evaluating the people involved is just as important as evaluating the opportunity itself.
Does This Really Deserve My Time?
This is probably one of the simplest questions on this list, but it has also become one of the most important.
There is always something else you could be doing. Someone wants a meeting. A new project sounds interesting. An email appears urgent. A potential opportunity lands in front of you unexpectedly. None of these things are necessarily a waste of time, which is precisely what makes prioritizing them difficult.
Earlier in my career, I thought time management was mostly about becoming more efficient, so I could fit more into the day. I have gradually realized it is often about deciding what shouldn’t be on my schedule at all.
Saying no to something obviously bad is easy. Saying no to something potentially worthwhile is much harder because there is always a lingering question about what might happen if you pursue it.
I still get that decision wrong sometimes. What has changed is that I no longer automatically view saying no as missing an opportunity. Sometimes saying no is simply how you protect enough time to do the things you have already committed to properly.
Am I Solving the Problem or Making It Disappear for Now?
Working with properties has made me particularly aware of the difference between fixing a problem and temporarily hiding it.
Imagine finding a water stain on a ceiling. Someone repairs the area and repaints the ceiling. A few months later, the stain returns in exactly the same place. You can paint it again, but at some point you have to stop asking how quickly the ceiling can be repaired and start asking where the water is coming from.
I have seen versions of that same situation in business. A process repeatedly breaks down, so someone manually fixes it every time. A communication problem keeps causing confusion, so another meeting gets scheduled. Someone becomes overwhelmed, so work gets shuffled around without anyone asking why the problem keeps happening.
Temporary solutions are fine when a situation requires an immediate response. The mistake is allowing a temporary solution to become permanent without realizing it.
I wish I had started asking, “Why are we dealing with this again?” much earlier in my career.
What Happens If This Takes Twice as Long as Expected?
I was probably much more optimistic about timelines when I was younger. I would look at a project, estimate how long it should take, and assume that a reasonable plan would produce a reasonably predictable schedule.
Experience has made me leave more room for reality.
Projects become complicated. Approvals take longer than expected. Someone changes their mind. A seemingly minor issue leads to another issue that nobody anticipated. I have seen enough of those situations that I now like to ask what happens if something takes twice as long as originally planned.
Would the project still make sense? Would everyone involved still have the patience to finish it properly? Would I still want to be working on it?
I do not think asking those questions is pessimistic. In many ways, it makes me more comfortable moving forward because I have considered a version of events that is less convenient than the one everyone hopes will happen.
Am I Actually Listening?
This is something I have thought about much more since becoming a SCORE mentor.
When someone starts describing a business problem, it can be tempting to start forming an answer before they finish explaining the situation. Experience can make that temptation even stronger because you hear something familiar and assume you already know where the story is going.
Then the person adds one more detail, and suddenly the situation is completely different.
Working with entrepreneurs has reminded me that advice is not particularly useful if it answers the wrong question. I have learned to give people more room to explain what is happening before I decide what I think.
That lesson applies well beyond mentoring. Employees, residents, business partners, and people you meet in a community will often tell you something important if you give them enough time to finish what they are trying to say.
I wish I had become a more patient listener earlier.
Do I Really Need to Decide Today?
Some situations require speed, and other times delaying a decision creates more problems than it solves. However, I no longer believe that being decisive always means deciding quickly.
Earlier in my career, I sometimes felt that if I understood the basic facts, there was little reason to wait. Today, I am much more comfortable allowing an important decision to sit overnight when circumstances permit.
Sometimes I will revisit the information the next morning. I might walk a property again or have another conversation with someone whose perspective I trust. I am not waiting because I expect perfect certainty to suddenly appear. Usually, it will not.
What I want is enough distance to tell whether I genuinely believe in the decision or whether I was simply excited about it in the moment.
I have had ideas that seemed much less appealing the next morning. I have also had decisions that felt even more obvious after giving them some time. Both outcomes have been useful.
What Will I Think About This Five Years From Now?
When I was younger, five years seemed like an enormous amount of time. After being in business for a while, you realize how quickly five years can pass.
That realization has changed the way I think about decisions. I am more likely to ask whether a relationship, project, or decision will still matter several years from now. I think about whether I am solving something meaningful or simply responding to whatever feels urgent today.
I do not ask those questions because I have become less ambitious. I think I have simply become more selective about where I put that ambition.
Experience has not given me all the answers. If anything, it has made me more aware of how much cannot be predicted. People surprise you. Markets change. Projects take unexpected turns, and priorities that once seemed incredibly important sometimes become almost irrelevant with time.
What experience has given me is a better set of questions.
I still make mistakes. I still occasionally spend too much time on something that turns out not to matter. I still misjudge people, timelines, and priorities. I do not think experience ever completely eliminates those mistakes.
The difference is that I am now much more comfortable stopping before I move forward and asking whether something truly deserves my time, whether I understand the people involved, and whether I am solving the real problem.
Those are questions I wish I had asked more often at the beginning of my career.